Making History
Jackie & Phil

A fabulous celebration at one family’s historic coastal estate created memories that will last a lifetime.

Story by Mimi Pinette
Photography by Leah Fisher Photography

Philip Smith and Jacqueline Press met in 2004 as freshman at Dickinson College in Carlisle, Pennsylvania. They were a part of a group of a dozen best friends who remained close after graduation—regularly meeting up for long weekends together. It just so happened that on one of those long weekends in 2012, Philip and Jackie became more than just friends.
“Philip and I both joke around that we are the male/female version of one another,” Jackie says. “Whoever said opposites attract was wrong…in our case at least!”
Jackie is from New Jersey and Philip grew up in Baltimore, Maryland. Philip decided to propose to Jackie in a place that is very special to his family—Tenants Harbor, Maine. Philip spent every summer with his family in this coastal village, and decided to surprise Jackie with a proposal on her family’s first trip to Maine.
Following a family wedding in Boston, Jackie and Philip dropped her family off at the East Wind Inn in Tenants Harbor where they would be spending the weekend. The couple made plans to pick them up in the family boat for a picnic of lobster rolls on an island a little later on that day. But when Jackie and Philip left the dock, she realized he wasn’t steering them in the direction of the inn. “When we got to the mouth of the harbor, right in front of Tenants Harbor Lighthouse, the boat just stopped,” Jackie says. Philip told her that he thought there was seaweed caught in the motor and asked her to take the wheel so he could check. When she turned around to help, Philip was on one knee with a ring box in his hand.
Getting married in Tenants Harbor was an easy decision. “Philip and his family have been summering there since the early 1900s,” Jackie says. “Our first trip to Maine together was Fourth of July weekend in 2012, which we knew would be the first of many. We knew before we got engaged that when we did get married, it would be in Maine.”
The couple, who live in Maryland, planned their wedding ceremony on the lawn of the East Wind Inn overlooking Tenants Harbor. The spot was perfectly situated across the harbor from the Smith family home, which was the site of the couple’s reception. The back lawn of The Hart House was the perfect location for dinner and dancing under the summer night sky.
Coastal Maine was the inspiration behind the couple’s celebration. Jackie and Philip sent guests lobster bibs in their wedding invitations and included uniquely Maine essentials in their welcome bags, including whoopie pies and Tom’s of Maine toothpaste! Their reception tables featured lighthouse lanterns and nautical knots, and L.L. Bean Boots did double duty as wildflower vases. Guests were directed throughout the day with custom signs made by their best man and his wife. These signs were created from driftwood and lobster buoys that Jackie and Philip collected. The couple even had tiny lobster buoys, hand painted to match the Smith family lobster trap buoy colors, as escort card holders. 
On the morning of their wedding, Jackie and Philip got ready separately before joining for their ‘first look.’ The wedding party and family members then boarded two sprinters that motored them to Marshall Point Lighthouse in nearby Port Clyde for formal photos. Upon their return, everyone hung out in the Quarry Tavern at the inn before the ceremony.
Since Jackie is Jewish and Philip is Episcopalian, they had an interfaith ceremony with a Rabbi and a Reverend. “Our wedding ceremony was perfect,” Jackie says. “My most vivid memory of the day was walking down the aisle with my dad. I was flooded with so many different kinds of emotions and totally overwhelmed—in the very best way.”
Jackie, Philip, their bridal party, and families, hopped on the Smith family boat, the Dyon, and motored across the harbor to The Hart House for the reception. Everyone enjoyed a cocktail hour with a jazz trio before dinner. “We danced the night away!” Jackie says. “My father surprised everyone with an outrageous fireworks display. Everyone was blown away. It was the perfect end to the absolute best, most special, night of our lives.”  
In Jackie's Words
I’m so glad that…we buried that bottle of bourbon in The Hart House field a month before the wedding! Southern tradition says that if you bury a bottle of bourbon at the wedding site, it won’t rain on the wedding day. According to many believers, this must be done exactly one month before the wedding, the bottle must be completely full, and it must be buried upside down to ensure maximum weather persuasion.
One of my favorite moments was…sailing from the wedding ceremony to the wedding reception at The Hart House. As we motored across the harbor, all of the other boats anchored in the harbor started blowing their horns. It was definitely one of the highlights of the day.
My advice to other couples is…the same advice Philip gave me throughout our wedding planning process when I would get worked up over the small stuff: Don’t lose sight of what the day is really about.
Maine Vendors
Day of Coordinator: The Purple Orchid, Brunswick
Ceremony Venue: East Wind Inn, Tenants Harbor
Reception Venue: The Hart House, Tenants Harbor
Caterer & Bakery: Trillium Caterers, Belfast
Reception Tent: Wallace Events, Rockland
Florist: Seasons Downeast Designs, Rockport
Hair & Makeup: Alison Bogannan at Artisan Hair Studio, South Portland
Nails: Rheal Day Spa, Rockland
Ceremony Music: Midcoast Music Academy, Rockland
Escort Lobster Buoys: Maine Wedding Artist, Camden
Reception Entertainment: The Waiters, Portland
Transportation: Country Coach Charters, Nobleboro
Fireworks: Central Maine Pyrotechnics, Hallowell